As she sits in the Rose cafe in Venice, California, it does not look as if a quarter of a century has passed since Liz Phair’s debut album, Exile in Guyville, made her rock’s voice of third-wave feminism. But, a quarter of a century on, as it is remastered and reissued to mark its 25th anniversary, men are still excluding women from power, reducing them to sexual objects and demeaning their modes of expression. It’s Guyville redux, only this time it is not just the hipsters in Phair’s indie-rock scene of early 90s Chicago. It is the man in the White House.

“You could not have given us a bigger middle finger,” says the Los Angeles-based singer-songwriter, referring to how Trump’s election appeared to women. “It changed what I needed to do in the world, who I wanted to be and what I wanted to put out there.” She is working on new material, after the events of November 2016 led her to abandon the songs she had been writing with Ryan Adams. “Post-election, there was a lightness that didn’t fit any more,” she says.

Music aficionados – and women who came of age with her acid-tongued confessionals – have celebrated Phair’s return. Yet, thanks to her unexpected career turns since Guyville, she remains largely unknown to a generation smitten with Solange, Lana Del Rey and others whose ability to sing frankly about sexual power relations is in some ways beholden to Phair’s trailblazing provocations. On songs such as Polyester Bride and Flower, she used graphic language to challenge the emotive equity of what is now called friends with benefits, or to mock the “slut-shaming” of sexually active women long before this was even a term.

Exile in Guyville … ‘My mother made sure I knew the contributions and powers of women throughout history.’

Later, her frustration with the hypocritical limitations of “alternative” rock led her to experiment with fashion and music choices that were seen as more mainstream; moves that alienated her from some of her initial fanbase. She was also raising a son – and she disappeared into motherhood.

Phair marvels at the creative feel of the bustling, hustling Rose cafe, a few miles from the upmarket seaside community of Manhattan Beach that she has called home for two decades. “The creative world is where I belong,” she says. “My life hasn’t been easy and it has been very up and down, but, as my mom likes to say: ‘You’re never happier than when you’re singing some song.’”

In her 51 years, Phair has known her share of different communities. She was born in Connecticut, where she was given up by her biological mother and adopted by a medical student at Yale and his wife. Along with her older brother, Phillip, they lived in Cincinnati, Ohio, for a time, then spent a year in Sheffield while her father was on sabbatical. Experiencing a different culture was transformative for Phair, making her a lifelong Anglophile. “I’ve seen every cathedral, manor house and castle. My mom packed about five years of living into that one.”

She is also obsessed with the British royal family and traces that not so much to her childhood year in the UK, but to her status as an adopted child who, out of love and respect for the man and woman who raised her, has never sought out her birth parents. “Of course, you want to know where you came from, and you’d like to see people who look like you. I want to marry into [the royal] family because you can trace everything back.”

The Phair family then settled in a wealthy suburb of Chicago, the kind of neighbourhood depicted in John Hughes movies that seem to offer a seemingly perfect existence but under whose surface roils social dysfunction. “Those kinds of places were built probably for the express purpose of raising children in a safe environment; it was a conspiracy to keep us safe, to make us into model citizens.”

The pressure to succeed was oppressive. Eating disorders abounded. Three friends killed themselves. “That explains why I have this impulse to share, to be honest and unveil stuff – because that area was like: ‘No, you have to be perfect.’” She rebelled, refusing to take the home economics course required of female students. She stayed out, smoked cigarettes and pot, and drank.

Phair recognises that her decision to opt out was cushioned by the safety net of her privileged upbringing. “My father made sure that I could speak at the dinner table. My mother made sure I knew the contributions and powers of women throughout history. I was raised to feel a sense of my own value.” She managed to get a diploma despite her defiance against gender discrimination in education, and she returned to Ohio to study at Oberlin College, where she recorded songs for the first time, secretly in her dorm room.

Men were the gatekeepers. I was tired of being the girlfriend of the guy in the band

Liz Phair

After graduating, she moved to San Francisco, where a friend from Oberlin, the musician Chris Brokaw, encouraged Phair to record more. Thus began the Girly-Sound tapes, released for the first time with the Guyville reissue: lo-fi recordings of raw, unedited, very personal material, such as Fuck and Run, a song that presaged the freedoms – and frailties – of today’s hook-up culture. Her guitar-playing and lyrics were dense, but the singing and point of view were in your face and eminently relatable. The songs were about disappointment and estrangement, about the failure of feminism to resolve the most basic of bedroom power struggles. “Those songs about the new flush of love, how awesome it is? I want to write that, but I just don’t,” she says. “I don’t turn to the guitar when I’m really happy. I’m a dark writer.”

Phair then returned to Chicago and continued to live the itinerant life of a wannabe artist. But she quickly learned what so many women involved in supposedly progressive communities discover: same shit, different soundtrack. Increasingly irritated by the hipper-than-thou arrogance of Chicago’s testosterock scene, called Guyville by one resident male, she decided to speak out.

“There was a very strong sense of: I’m tired of giving up the patriarchy, and the mainstream, just to have it recreated in this sub-sect of alternative music,” she says. “Men were the gatekeepers. They ran all the equipment and the labels … I was tired of being the girlfriend of the guy in the band, I was tired of hearing that my musical tastes suck.”

Phair knew just what she wanted to make: a riposte to the Rolling Stones’ Exile on Main Street. Just like that rock classic, Exile in Guyville would be a double album. It’s a near-perfect record: 18 songs that capture a woman learning to navigate the adult world on her own and discovering that her fight for free choice did not end with home economics.

Guyville was an immediate critical favourite and college-radio hit, though it didn’t chart. She followed with Whip-Smart, a decent, but not outstanding, album, which landed her on the cover of Rolling Stone magazine and earned her criticism from fans and feminists for posing in a slip, sans guitar. She stands by the decisions she has made: “I please myself,” she says. “When I make music I don’t worry about people thinking it’s cool or not. But it’s scary how the male perspective can shape women without them even knowing.”

Phair embraced pop, but the sharp-witted tongue that defined earlier work did not necessarily endear her to the mainstream fans she was seeking and she struggled with her next four albums. Though she scored her biggest hit in 2003 with Why Can’t I?, the idea of the Joni Mitchell of her generation hiring writing and production team the Matrix struck many as unseemly – shouldn’t the verbally and melodically adept Phair be writing songs for the hit-makers, not the other way round? She would have loved to simply write and never perform again, but that line of work hasn’t panned out. “I think I’m too weird,” she says. “I think my songs aren’t straight enough.”

Besides, Phair had been focused on another endeavour: life as a divorcee and raising her son, Nick. She wanted to give him the normal, suburban experience she had once resisted – with mixed results. “I was just Mom, but I’m not sure in retrospect if he wouldn’t have preferred a little more rock star, a little less Mom.”

Her son is now on his own track, and she remembers a time he flew to Japan with a high school group. After leaving him at the airport, “I went home and realised my son was crossing an ocean without me, and had this deep … it wasn’t sad crying, it was a one-of-a-kind cry, and it felt primal. I felt as if a thousand women had cried like me before – proud that the job was done, but feeling that invisible umbilical cord finally cut.”

And so Phair has found herself revisiting the soundtrack of her own flight from her cocoon. Current events have given her a renewed sense of purpose. Her first book, a collection of stories about touchstone moments of trauma and change in her own life, will be published in the autumn. Shows for her tour sold out in seconds. Once again, circumstances – the extremity of the new political administration – are driving her out of her bedroom. “It’s obscene!” she says, specifically referencing the praise that the US attorney general, Jeff Sessions, lavished upon the Philippines for slaughtering drug dealers, but speaking more generally about the extreme right turn her country has taken. “We’ve reached the level of obscenity.”

So once again Phair is crafting her own idiosyncratic protest music, trying to process it all. “It was such a big blow that it takes a minute to run through the metabolism to come out. The profound stuff will have to be digested slowly,” Phair says. “But we all just have to come with guns blazing. Actuate now, even in a most imperfect way because the people that are quieter need to get louder.”

Girly-Sound to Guyville – 25th Anniversary Box Set by Liz Phair is released on 4 May. Evelyn McDonnell is the editor of Women Who Rock: Bessie to Beyoncé, Girl Groups to Riot Grrrl, to be published in autumn 2018.